Head-mounted display units allow users to mount mobile computing devices on or around their head, enabling the user to transport and utilize advanced technologies with greater ease and flexibility. Head-mounted display units also enable a user to have interaction with the technology while otherwise remaining engaged in other tasks. For instance, head-mounted display units can be voice activated and hands-free, so that users are able to focus on other more “physical” tasks, or simply desire a more hands-free computing experience. However, head mounted display units have been traditionally limited to being used in conjunction with a limited number of headwear form-factors. In some instances, head mounted display units can be designed for securement to pre-existing fastener elements found on headwear, such as those typically found on hard hats. In the alternative, elastic straps may be employed to secure the head mounted display unit to the user's head, though some may find these straps to be unappealing. Additionally, headwear utilized for head mounted display units do not always provide users with an intuitive, natural, and comfortable fit. Therefore, a head mounted display mounting assembly that can safely secure the head-mounted display unit to alternative types of headwear, in addition to conventional form-factors, would be beneficial.